Cesium carbonate → HCID 67995507, compound

HRID 2042934Notes

Reaction equation

HRID 2042934 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22](Br)=[C:21]([CH2:26][C:27]3[S:28][C:29]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)=[CH:30][N:31]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2].[CH:42]1(B(O)O)[CH2:44][CH2:43]1.F[B-](F)(F)F.C1([PH+](C2CCCCC2)C2CCCCC2)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@H:8]([C:19]2[CH:24]=[CH:23][C:22]([CH:42]3[CH2:44][CH2:43]3)=[C:21]([CH2:26][C:27]3[S:28][C:29]([C:32]4[O:33][CH:34]=[CH:35][CH:36]=4)=[CH:30][N:31]=3)[CH:20]=2)[O:7][C@@H:6]1[CH2:37][O:38][C:39](=[O:41])[CH3:40])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 11710396Tricyclohexylphosphonium TetrafluoroborateHCID 86680890HCID 86680890, compound

Product 1

HCID 67995507HCID 67995507, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

The bromide 58 (300 mg, 0.46 mmol) was added to a microwave reaction tube containing cyclopropylboronic acid (86.9 mg, 1.01 mmol), palladium(II) acetate (31 mg, 46 μmol), tricyclohexylphosphonium tetrafluoroborate (68 mg, 0.18 mmol) and cesium carbonate (601 mg, 1.84 mmol) in dioxaone (5 mL). The capped reaction tube was placed in a microwave reactor and the mixture irradiated at 150° C. for 25 min. After dilution with EtOAc, the organic layer was washed with water and brine prior to drying over anhydrous MgSO4. After filtration and concentration under reduced pressure, the residue was purified by silica column chromatography to provide the cyclopropane 60 (56 mg, 20%) as a yellow oil. MH+612.

Workup

  1. customThe capped reaction tube
  2. customwas placed in a microwave reactor
  3. customthe mixture irradiated at 150° C. for 25 min
  4. washAfter dilution with EtOAc, the organic layer was washed with water and brine
  5. dry with materialto drying over anhydrous MgSO4
  6. filtrationAfter filtration and concentration under reduced pressure
  7. customthe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-d7703b95dc4148438ccf63996aaedef8
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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